Cheap flights from Orlando to Chicago from $58

Round-trip
1 adult
Economy
From?
To?
Tue 5/31
Tue 6/7

Deals available from 900+ travel sites.

Flight information for Orlando to Chicago

Find info about flight duration, direct flights, and airports for your flight from Orlando to Chicago

Best Price Found

$58

Fastest flight time

2h 41m

Direct flights

Mon, Tue, Wed, Fri, Sat and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Orlando in the past 72 hours is $58. The best round-trip flight deal from Orlando to Chicago found on momondo in the last 72 hours is $152.
The fastest flight from Orlando to Chicago takes 2h 41m
Direct flights go from Orlando to Chicago on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. The only airline offering direct flights is Allegiant Air.
There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

How to get the cheapest flight ticket from Orlando to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly from Orlando to Chicago?

August

The cheapest time of year to fly to Chicago from Orlando is August. Most expensive is October

What is the cheapest airline that flies to Chicago from Orlando?

Juneyao Airlines

Allegiant Air, Frontier, and Juneyao Airlines are the most popular carriers operating from Orlando to Chicago

What is the cheapest Orlando to Chicago flight route?

Orlando - Chicago O'Hare Intl

Fly from Orlando to Chicago O'Hare Intl for the best Orlando - Chicago flight prices

How far in advance should you book Orlando to Chicago flights?

13 days before

The cheapest time to buy a flight from Orlando to Chicago is approximately 13 days to departure

Orlando Airport (MCO) to Chicago O'Hare Intl Airport (ORD)$166
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Orlando Airport (MCO) to Chicago Midway Airport (MDW)$225
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Orlando Sanford Intl Airport (SFB) to Chicago Greater Rockford Airport (RFD)$176
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Orlando Airport (MCO) to Chicago Greater Rockford Airport (RFD)$483
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When you’re planning your trip from Orlando to Chicago, the most popular airport-to-airport route is Orlando Airport to Chicago O'Hare Intl Airport. You may be looking for an airport near Orlando Airport to depart from when traveling to Chicago and luckily, there are options! You can try Orlando Airport which is located in Orlando or Orlando Sanford Intl Airport which is located in Orlando. If you are looking for alternate airports to fly into when traveling from Orlando, you can try Chicago Midway Airport or Chicago Greater Rockford Airport which are located in Chicago and Chicago respectively. In May, $166 is typically the cheapest round trip price you’ll find from Orlando to Chicago which you can find when you fly MCO — ORD.


Easily compare round-trip flights from Orlando to Chicago

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Orlando to Chicago by changing tabs
Spirit Airlines
Aug 17
MCO12:30 pmOrlando
3h 08m
ORD3:38 pmChicago O'Hare Intl
Aug 24
ORD1:30 pmChicago O'Hare Intl
5h 00m
1 stop
MCO6:30 pmOrlando
Allegiant Air
Aug 3
SFB2:45 amOrlando Sanford Intl
2h 39m
RFD5:24 amChicago Greater Rockford
Aug 5
RFD4:59 amChicago Greater Rockford
2h 27m
SFB7:26 amOrlando Sanford Intl
Multiple Airlines
Jun 7
MCO4:39 pmOrlando
3h 00m
ORD7:39 pmChicago O'Hare Intl
Jun 8
ORD7:10 amChicago O'Hare Intl
5h 11m
1 stop
MCO12:21 pmOrlando
Frontier
Jun 9
MCO2:08 amOrlando
3h 09m
ORD5:17 amChicago O'Hare Intl
Jun 9
ORD4:00 pmChicago O'Hare Intl
2h 59m
MCO6:59 pmOrlando
Delta
Sep 23
MCO2:10 amOrlando
7h 34m
1 stop
MDW9:44 amChicago Midway
Sep 26
MDW9:00 amChicago Midway
5h 37m
1 stop
MCO2:37 pmOrlando
Spirit Airlines
Aug 16
MCO12:30 pmOrlando
3h 08m
ORD3:38 pmChicago O'Hare Intl
Aug 23
ORD6:38 amChicago O'Hare Intl
2h 47m
MCO9:25 amOrlando

Find the cheapest one-way flights from Orlando to Chicago

If you're looking for one-way flights from Orlando to Chicago, view some of our deals below provided by Allegiant Air and Spirit Airlines
Allegiant Air
Aug 3
SFB2:45 amOrlando Sanford Intl
2h 39m
RFD5:24 amChicago Greater Rockford
Spirit Airlines
Jun 21
MCO5:58 pmOrlando
13h 19m
1 stop
ORD7:17 amChicago O'Hare Intl
Multiple Airlines
Aug 23
MCO6:00 pmOrlando
16h 55m
1 stop
ORD10:55 amChicago O'Hare Intl

Search last-minute flights to Chicago from Orlando

Find and compare round-trip flight prices for your last-minute flight from Orlando to Chicago
Allegiant Air
Jun 1
SFB10:54 amOrlando Sanford Intl
2h 42m
RFD1:36 pmChicago Greater Rockford
Jun 22
RFD4:08 pmChicago Greater Rockford
2h 33m
SFB6:41 pmOrlando Sanford Intl
Multiple Airlines
Jun 1
MCO4:39 pmOrlando
3h 00m
ORD7:39 pmChicago O'Hare Intl
Jun 8
ORD7:10 amChicago O'Hare Intl
10h 30m
1 stop
MCO5:40 pmOrlando
Frontier
Jun 1
MCO4:39 pmOrlando
3h 00m
ORD7:39 pmChicago O'Hare Intl
Jun 2
ORD12:56 pmChicago O'Hare Intl
2h 57m
MCO3:53 pmOrlando
Spirit Airlines
Jun 2
MCO1:15 amOrlando
3h 03m
ORD4:18 amChicago O'Hare Intl
Jun 2
ORD3:16 pmChicago O'Hare Intl
2h 43m
MCO5:59 pmOrlando
Multiple Airlines
Jun 1
MCO4:39 pmOrlando
3h 00m
ORD7:39 pmChicago O'Hare Intl
Jun 4
ORD2:20 pmChicago O'Hare Intl
2h 43m
MCO5:03 pmOrlando
Frontier
May 31
MCO4:39 pmOrlando
3h 00m
ORD7:39 pmChicago O'Hare Intl
Jun 2
ORD12:56 pmChicago O'Hare Intl
2h 57m
MCO3:53 pmOrlando

Best airlines flying from Orlando to Chicago

Compare and see reviews for airlines that fly from Orlando to Chicago with momondo
AirlineRatingFree CancellationPrice
Juneyao AirlinesPriceFrom $12Free CancellationRating
0.0
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Spirit AirlinesPriceFrom $43Free CancellationRating
6.2
6.4

Boarding

5.8

Comfort

6.9

Crew

4.8

Entertainment

5.1

Food

Reviews

Horrible experience

1 / 10
Search Spirit Airlines flights
FrontierPriceFrom $47Free CancellationRating
6.1
6.4

Boarding

5.8

Comfort

6.9

Crew

4.7

Entertainment

5.0

Food

Reviews

Nothing, the boarding process snd the baggage handling process for checking & pick up at destination was delayed and confusing

1 / 10
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Allegiant AirPriceFrom $72Free CancellationRating
7.1
7.4

Boarding

6.9

Comfort

8.2

Crew

5.5

Entertainment

6.2

Food

Reviews

Crew was professional. I liked the captain giving us occasional updates.

1 / 10
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American AirlinesPriceFrom $73Free CancellationRating
7.3
7.7

Boarding

7.2

Comfort

8.1

Crew

7.0

Entertainment

6.5

Food

Reviews

Entertainment is very limited. Location of the gate is not convenient. Passengers must take a shuttle bus. The rest was good.

1 / 10
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United AirlinesPriceFrom $78Free CancellationRating
7.4
7.6

Boarding

7.2

Comfort

8.0

Crew

6.9

Entertainment

6.7

Food

Reviews

Very smooth boarding, and excellent crew service. Food needs improving. Please provide eggs for breakfast. Also not enough water provided for this long flight. Crew needs to come around every 3 hours to offer water. Bigger size water bottles. Or provide a spigot to fill water bottles. Crew were always helpful and willing to provide water.

1 / 10
Search United Airlines flights
DeltaPriceFrom $88Free CancellationRating
7.9
7.9

Boarding

8.0

Comfort

8.3

Crew

7.7

Entertainment

7.3

Food

Reviews

One of the crew member weren’t to pleasant

1 / 10
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Spirit Airlines flights from Orlando to Chicago

Our best Spirit Airlines deals on Orlando to Chicago flight tickets
Spirit Airlines
Aug 17
MCO12:30 pmOrlando
3h 08m
ORD3:38 pmChicago O'Hare Intl
Aug 24
ORD1:30 pmChicago O'Hare Intl
5h 00m
1 stop
MCO6:30 pmOrlando
Spirit Airlines
Aug 16
MCO12:30 pmOrlando
3h 08m
ORD3:38 pmChicago O'Hare Intl
Aug 23
ORD6:38 amChicago O'Hare Intl
2h 47m
MCO9:25 amOrlando
Spirit Airlines
Aug 10
MCO12:30 pmOrlando
3h 08m
ORD3:38 pmChicago O'Hare Intl
Aug 17
ORD6:38 amChicago O'Hare Intl
2h 47m
MCO9:25 amOrlando

Frontier flights from Orlando to Chicago

Our best Frontier deals on Orlando to Chicago flight tickets
Frontier
Jun 1
MCO4:39 pmOrlando
3h 00m
ORD7:39 pmChicago O'Hare Intl
Jun 2
ORD12:56 pmChicago O'Hare Intl
2h 57m
MCO3:53 pmOrlando
Frontier
Jun 9
MCO2:08 amOrlando
3h 09m
ORD5:17 amChicago O'Hare Intl
Jun 9
ORD4:00 pmChicago O'Hare Intl
2h 59m
MCO6:59 pmOrlando
Frontier
May 31
MCO4:39 pmOrlando
3h 00m
ORD7:39 pmChicago O'Hare Intl
Jun 2
ORD12:56 pmChicago O'Hare Intl
2h 57m
MCO3:53 pmOrlando

  • Are airlines flying from Orlando to Chicago offering flexible cancellation due to COVID-19?

    Some of our partner airlines flying from Orlando to Chicago are adopting new policies due to the global impact of COVID-19. Some of the airlines that may be waiving their cancellation fees are Spirit Airlines, United Airlines, and American Airlines. You can search for the full list of airlines like Spirit Airlines that are offering this flexibility.

  • How far is Orlando to Chicago by plane?

    Chicago is 985.3 mi away from Orlando. 2h 34m is a normal flight duration for this route.



Alternative routes for Orlando to Chicago

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Fort Lauderdale to Chicago Flights
Fastest flight time3h 11m
Cheapest price$95
Tampa to Chicago Flights
Fastest flight time2h 58m
Cheapest price$133
Miami to Chicago Flights
Fastest flight time3h 20m
Cheapest price$115
West Palm Beach to Chicago Flights
Fastest flight time3h 15m
Cheapest price$280
Fort Myers to Chicago Flights
Fastest flight time3h 00m
Cheapest price$134
Jacksonville to Chicago Flights
Fastest flight time2h 32m
Cheapest price$234
Orlando to St. Louis Flights
Fastest flight time2h 21m
Cheapest price$120
Pensacola to Chicago Flights
Fastest flight time2h 34m
Cheapest price$326
Miami to St. Louis Flights
Fastest flight time2h 48m
Cheapest price$200
Fort Lauderdale to St. Louis Flights
Fastest flight time2h 53m
Cheapest price$188
Daytona Beach to Chicago Flights
Fastest flight time4h 29m
Cheapest price$433

Similar Orlando to Chicago flights

Flexible with your destination? Broaden your search and find flights similar to your Orlando to Chicago route

Why use momondo?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Orlando to Chicago. momondo saves you time and could save you money on your trip.

Flights from Orlando to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Orlando.

Price alerts on flights to Chicago from Orlando are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.


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Flexible Travel
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